Chapter 7 further develops the study’s critical juncture framework and justifies its extension to cases in South America. Drawing lessons from Eastern Europe, I begin by distinguishing between varying illiberal tendencies in Slovakia and Poland, based on which I offer new theoretical insights. As I elaborate sequences linking (1) illiberals’ divergent ability to be politically dominant back to whether neoliberal reform agents were social democrats or polarizing populists, and (2) contestatory versus moderate tendencies back to whether or not anti-neoliberal protest was institutionalized during critical periods of early market reform, I elaborate the argument about the durable effects of contingency associated with postcommunist junctures. I then make the case for applying the refined framework to South American cases. Here, I note some blind spots in scholarship on Latin American populism and highlight important commonalities between dynamics in Eastern Europe and the Andes. Next, I review the advantages of analyzing developments in Ecuador and Peru from a comparative perspective that is sensitive to both cross- regional and intra-regional patterns of similarity and difference. Ending with a discussion of the insufficiency of standard explanations of illiberal trends, the chapter sets the stage for the paired comparison that follows.